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Exploding pants is achieved by reverse pickpocketing a live grenade, mine or C-4 plastic explosive into an NPC's inventory and running away quickly to avoid being caught in the blast. A successful planting always kills the NPC.

As long as you remain [HIDDEN] and are not caught pickpocketing, it counts as a stealth kill so no other friendly NPCs will turn hostile and no Infamy will be gained with the NPC's faction. This means that the easiest way to complete this challenge is to stealthily blow up 25 unnamed friendly NPCs in friendly locations such as Crimson Caravan Company. Another option, Jacobstown, allows you to work on the Super Mutant Massacre challenge at the same time.

Frequent quicksaving is recommended as NPCs still have a chance to detect pickpocketing even with Sneak 100. Silent Running and health items are also recommended to minimize the chances of being caught in the blast.